Zebularine

Catalog No.S7113 Synonyms: NSC 309132

Zebularine Chemical Structure

Molecular Weight(MW): 228.2

Zebularine is a DNA methylation inhibitor that forms a covalent complex with DNA methyltransferases, also inhibits cytidinedeaminase with Ki of 2 μM in a cell-free assay.

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1 Customer Review

  • (A) Zebularine treatment suppresses fibre development in vitro. This figure shows that 0 day post anthesis (DPA) ovules cultured for 10 days exhibit different fibre lengths. Different concentrations of zebularine (20, 40 and 80 μM) were applied.

    Nucleic Acids Res, 2016, 44(9):4067-79.. Zebularine purchased from Selleck.

Purity & Quality Control

Choose Selective DNA Methyltransferase Inhibitors

Biological Activity

Description Zebularine is a DNA methylation inhibitor that forms a covalent complex with DNA methyltransferases, also inhibits cytidinedeaminase with Ki of 2 μM in a cell-free assay.
Features Very stable with half-life of ~44 h at 37°C in PBS at pH 1.0 and approx. 508 h at pH 7.
Targets
DNA methyltransferase [1]
(Cell-free assay)
Cytidine deaminase [2]
(Cell-free assay)
2 μM(Ki)
In vitro

Zebularine is a cytidine analogue containing a 2-(1H)-pyrimidinone ring, originally synthesized as a cytidine deaminase inhibitor. [2] Zebularine is shown to form a tight, covalent complex with bacterial methyltransferases. [1] In N. crassa, zebularine inhibits DNA methylation and reactivates a gene previously silenced by methylation. Zebularine is a global inhibitor of DNA methylation, similar to 5-Aza-CR, rather than a selective inhibitor. Zebularine induces the myogenic phenotype in 10T1/2 cells, which is a phenomenon unique to DNA methylation inhibitors. Zebularine reactivates a silenced p16 gene and demethylates its promoter region in T24 bladder carcinoma cells. Zebularine is only slightly cytotoxic to T24 cells. [3] Zebularine is preferentially incorporated into DNA and exhibits greater cell growth inhibition and gene expression in cancer cell lines compared to normal fibroblasts. In addition, zebularine preferentially depletes DNA methyltransferase 1 (DNMT1) and induces expression of cancer-related antigen genes in cancer cells relative to normal fibroblasts. [4]

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
human T24 cells M2DTb2Z2dmO2aX;uJIF{e2G7 M{m5VlExOCEQvF2= NHWx[Hg5KGSjeYO= MX3JcoR2[3Srb36gc4YheDF4IHflcoUh\XiycnXzd4lwdiCrbjDoeY1idiCWMkSgZ4VtdHNiYYSgNVAxKHWPIHHmeIVzKDhiZHH5d{BjgSC{ZXHsJJRqdWViUFPSJIlvKHC{ZYPlcoNmKG:oIEGwNEBuVSC2aIntbYRqdmV? M1W0[lE6ODB4M{iy
human HCT15 cells MXPGeY5kfGmxbjDhd5NigQ>? MmXoNVAxKM7:TR?= MmTpPEBl[Xm| M1H2WGlv\HWldHnvckBw\iCyMU[g[4Vv\SCneIDy[ZN{cW:wIHnuJIh2dWGwIFjDWFE2KGOnbHzzJIF1KDFyMDD1UUBi\nSncjC4JIRigXNiYomgdoVidCC2aX3lJHBEWiCrbjDwdoV{\W6lZTDv[kAyODBibV2geIh6dWmmaX7l NIfvWo4yQTByNkO4Ni=>

... Click to View More Cell Line Experimental Data

In vivo Zebularine is only slightly cytotoxic to tumor-bearing mice (average maximal weight change in mice treated with 1000 mg/kg zebularine = 11% [95% CI = 4% to 19%]). Compared with those in control mice, tumor volumes are statistically significantly reduced in mice treated with high-dose zebularine administered by intraperitoneal injection or by oral gavage. [3]

Protocol

Animal Research:[3]
+ Expand
  • Animal Models: male BALB/c nu/nu mice
  • Formulation: 0.45% saline
  • Dosages: 500 mg/kg, 1000 mg/kg
  • Administration: Intraperitoneal, oral
    (Only for Reference)

Solubility (25°C)

In vitro DMSO 46 mg/mL (201.57 mM)
Water 46 mg/mL (201.57 mM)
Ethanol Insoluble
In vivo Add solvents individually and in order:
Saline
30 mg/mL

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 228.2
Formula

C9H12N2O5

CAS No. 3690-10-6
Storage powder
Synonyms NSC 309132

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Tech Support

Answers to questions you may have can be found in the inhibitor handling instructions. Topics include how to prepare stock solutions, how to store inhibitors, and issues that need special attention for cell-based assays and animal experiments.

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Related Antibodies

DNA Methyltransferase Signaling Pathway Map

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID